4-Isopropoxy-2-(trifluoromethyl)phenylboronic acid → (+/-)-trans 2-[4-isopropoxy-2-(trifluoromethyl)phenyl]-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline

HRID 1836574Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[C:7]([O:9][CH:10]([CH3:12])[CH3:11])[CH:6]=[CH:5][C:4]=1B(O)O.Cl.Cl.COC1C=CC([C:28]2[CH:29]=[C:30]3[C:35]4=[C:36]([CH2:38][CH2:39][CH2:40][N:34]4[CH2:33][C@@H:32]4[CH2:41][NH:42][CH2:43][C@@H:31]34)[CH:37]=2)=C(C(F)(F)F)C=1>>[CH:10]([O:9][C:7]1[CH:6]=[CH:5][C:4]([C:28]2[CH:29]=[C:30]3[C:35]4=[C:36]([CH2:38][CH2:39][CH2:40][N:34]4[CH2:33][C@@H:32]4[CH2:41][NH:42][CH2:43][C@@H:31]34)[CH:37]=2)=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:8]=1)([CH3:12])[CH3:11]

Participants

Reactant 2

HCID 220218424-Isopropoxy-2-(trifluoromethyl)phenylboronic acid

HCID 131724531(+/-)-trans-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline, bis-hydrochloride salt

Product 1

HCID 60088317(+/-)-trans 2-[4-isopropoxy-2-(trifluoromethyl)phenyl]-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline

Procedure

Using 2-trifluoromethyl-4-isopropoxyphenyl boronic acid and following the procedures described in EXAMPLE 34, (±)-trans tert-butyl 2-bromo-5,6,8a,9,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-10(8H)-carboxylate from EXAMPLE 7, Part A was converted into the title compound of EXAMPLE 35 as a yellow semi-solid. 1H NMR (500 MHz, CDCl3) δ 1.26 (s, 1H), 1.30 (d, 6H, J=6.1 Hz), 1.85-2.05 (m, 2H), 2.15 (m, 1H), 2.74 (m, 4H), 2.96 (t, 1H, J=7 Hz), 3.23 (m, 1H), 3.32 (m, 4H), 3.57 (t, 1H, J=7 Hz), 4.58 (sept, 1H, J=6.1 Hz), 6.59 (s, 1H), 6.77 (s, 1H), 6.99 (dd, 1H, J=2.5, 8.4, Hz), 7.18 (s, 1H), 7.24 (m, 1H). LRMS (ES)+: 417 (M+H)+.

Sources & evidence

ORD record: ord-8741c1195f434cf1af236ea3202ade4e
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777406B2

Reaction notes

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